Plastifier for cellulose derivatives and resin compositions



Patented Oct. 4, 1 932 omrafsTATEs,

PATENT OFFICE,

W L IAM Eisner Moss Ann BLAJNGHE BABETTE WHITE, or CUMBERLAND, MARYLAND, J AssIeNoRs TO c LANEsn CORPORATION or AMEnIoA, A CORPORATION or DELA- M No Drawing.

This -inventionrelates to the production of films, plastics and coating compositions,

suchas lacquers, containing cellulose derivatives, resin and plastifiersf ,A particular object. is to providefplasticizers for toluene sulphonamide-formalde- .hyde resin and cellulose acetate compositions.

In the use of cellulose derivatives such as cellulose acetate for the production of plastics and lacquer, the plastic composition or the film forming constituents of the lacquer usually consist of the cellulose derivative, one or more plastifiers'and one or more. resins, In the preparation of a pigmented lacquer film, the proportion of either the plastifiers alone'or of the resin alone may be greater g'dlthan that of the cellulose derivative. For the preparation of auseful lacquer film, it is necessary that all of the components thereof should be mutually compatible or form a clear homogeneous solid solution inthe ifi final lacquer film.

It is a matter of general observation that when the cellulose derivative is compatible with the resin alone and with the'plasticizer alone, it will be compatible with a mixture 36 0f plastifier and resin. However, there are jcertain exceptions to this rule, and it is an important matter in the art of making lacquer, to know to what extent the various three component mixtures of cellulose ester, resin and plasticizer are completely compatible.

Inthe preparation of lacquers containing organic derivatives of cellulose such as cellulose acetate, the formulationbecomes much more diflicult than with other cellulose dew rivatives, because cellulose acetate is compatible with only a limited number of resins and also with fewer plastifiers than other cellulose derivatives. When it is desired to put both a plastifier anda. resin with the acetate in the relatively large quantities as demanded by alacquer, it is found that the number of entirely compatible compositions of cellulose acetate, resin and plasticizer are very limited. Ina pigmented lacquer, the finely divided pigment in suspension throughout the lacquer PLASTIFIER r03 cELLU osE DERIVATIVES AND RESIN ooivrrosrrrons Ani als filed August 16; 1928. Serial No. 300,152.

introduces further complications and a three component mixture of cellulose acetate, resin and plastifier, which gives a clear homo geneouslacquer film, may have its mutual compatibilitydestroyed, so that one or other of the components separates out when a pigment is ground in Withthe clear lacquer.

We have found that compositions containing cellulose acetate and toluene sulphonamide-formaldehyde resin are particularly ,diificult to plastify. Some of the commonly used pl'astifiers for cellulose acetate, such as diethyl phthalate and tricresyl phosphate are quite unsuitable for use with a mixture of cellulose acetate and toluene sulphonamide formaldehyde resin. The addition of such plastifiers to the acetate-resin mixture even in such small proportion as 10% of the weight of the film forming materials, causes the lacquer film made from it to show a partial separation or bloom 'ofone of the components onthe surface of the film, This separation doesnot always'appear during the drying ofthe film but maybe delayed one or two days." It is also more pronounced when some pigments, such as Prussian Blue, are in the film thanwith others, such as chrome yellow. As a result of this separation or blooming, the films are unsatisfactory and worthless in' appearance, and have poor outdoor resistance. a i a We have found that certain other plas tifiers are quite suitable as plastifiers, and are compatible with the cellulose acetateresin mixture in large proportions and have the usual beneficial effects of a plastifier or softener on the film. Q

In accordance with our Tinventiomwe preparecoating or plastic compositions containing organic derivatives of cellulose, resin of the toluene sulphonamide type, and a plas tifier compatible therewith. Examples of such compatible. plastifiers are diphenylol propane, mono methyl xylene sulfonamide, ethyl toluene sulfonamide and triacetin.

By organic derivative of cellulose we mean organic esters of cellulose, such as cellulose acetate, cellulose propionate, cellulose formate or cellulose butyrate and cellulose g l -l.

ethers, such as methyl cellulose,'ethyl cellu lose, benzyl cellulose.

'pl c tio l-ii x e v Suitable low medium and/or high boiling solvents may be added. and other reslns, both The resin of the toluene sulphonamide type may be formed by heating toluene sulphon amide with an aldehyde such as formaldehyde or other compounds'having a mobile methylene group, 7 This resin may bejforme'd by heating e'qui mole'cular proportlons oi;

0., as described in our .co;-p.endi'ng application #300,15 filed on even'datef'herewith; The

resinflmay alsjobe prepared by" condensing.

toluene sulphonamid'e land-,formaldehyde in the presence of urea, as described in said I natural resins or'synthetic resins, such as phenol-formaldehyde resin, diphenylol pro pane-formaldehyde, or phenol-furfural resin= may be added Alsofirei retardants, es-i 'l pecially the bromine derivatives'of organic compounds,- such; as brominated tricresyl phosphatemay be added if desired. iPig-- ments: and dyesmay be incorporated when; I

, these'compatible plastifiersare used.

In order to further illustrateour invention,-- I

.triacetin, diphenylol propane, monom'eth'yl 'phona inide;

-maldehyd e, resin, and a; plasti'fier selected from the group consisting of. triacetin, 1diphenylol "propane, monomethyl' xylene sulphonamide and ethyl toluene sulphonamide.

lose acetate, a toluene isulphonamide-alde hyde'resin, and a plastifier selected from V the group consisting of triacetin, diphenylol propane, monomethyl xylene sulphonamide and ethyl toluene sulphonamide.

2. A coating composition containing an organic derivative of cellulose, a toluene sulphonamide-formaldehyde resin, and a plastifier selected from the group consisting of 7 Xylene sulphonamide and ethyl toluenesul- 7 A coating composition containing cellulose'* a'cetate, a" toluene sulphonaniide'-for-v composition of matter'containing an organic derivat ve of cellulose, at'ol'uene sulfonamid-aldehyde resin, andaplastifier selected from the group consisting of triacetin,

diphenylol propane, monomethyl x lene sul-o fonamid'a'nd ethyl toluene sulfonamid.

In testimony whereof, we have hereunto subscribed our names. 7 v

WILLIAM HENRY MOSS. s BLANCHE the following specific examples of film-formingcompositionsraregiven: 7

i V E pl s is I 1 'Parts Cellulose acetate; i i- ;i i r Toluene sulphonamide r esin- 20H I Diphenylol propane 20' Pigment; s- 10 Acetone-; i; i ;1 "Alcohol 1; 1 i 50.

Di'acetone -alcohol; i

I. H. .1 ,"i t L- Cellulose- .acetate i ;1-10 Toluene sulphonamide resi11 .12.5

Mono methyl Xylene sulphonamideiu; 8 V Acetone 100 "Ewamplelll -Pa'rts; Cellulose acetate i n1 '10v V I Toluene sulphonamide resin H 5 Triacetin v- --l.-'-----':,--- .3 Acetonen;; -i 100 E thyl acetate- 501 Benayl'alcohol 5 E It is to be understood that theforegoing detailed description is given merely by wayof example,,and that many" variations maybe -,--."-made ther-einwithout departing from the spiritQof our, invention. f V

H Havingndescribed our lllVQIllJlOIl,W1l3J-t we 7 claim and desire to secure by Letters Patent,

15": 1. A coating composition containing cellu- 

